The Return of the Preppy Honeymoon
From Palm Beach to Nantucket, the mid-20th-century WASP aesthetic is making a resurgence.
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Just ask W, Elle, and even the Wall St. Journal: Preppy is back, bigtime. Slightly tweaked, the mid-20th-century WASP aesthetic has been resurrected, and the corresponding watering holes of Palm Beach, Nantucket, Bermuda, and Newport are likewise experiencing a renaissance. Here’s our honeymoon guide to the resorts where style icons like Jackie Kennedy, C.Z. Guest, and Sister Parish made pink and green the unofficial preppy flag. La plus ça change.…
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Palm Beach
The resort town that gave birth to Lilly Pulitzer has seen a record number of new hotels and restaurants open in the past few years. Old Guard clubs like the Everglades and Bath & Tennis remain as stodgy as ever, but the surrounding area has gotten a reboot, and what’s not to like about white-sand beaches, international polo, and some of the best shopping in the world?
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The White Elephant
This outpost of the Nantucket gem is equally stylish, housed in a Mediterranean-style hotel built in the 1920s. The lobby fireplace and Carrera marble remain but are beautifully updated with contemporary art and furnishings. Located on Sunset Avenue in the center of town, the 13 rooms and 19 suites all have outdoor space, and there’s an offshoot of the über-chic sushi-and-burger joint Lola 41.
Eat
Swifty’s at the newly reimagined Colony Hotel is a white-hot spot with the same amazing food as its New York counterpart.
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The presidential yacht, the Honey Fitz, is now available for charters through the Pelican Club in Jupiter, while shopping on Worth Avenue remains one of the headiest retail highs in the world.
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Bermuda
Mark Twain said, “You can go to heaven if you want. I’d rather stay in Bermuda.” The easy-to-reach paradise off the coast of South Carolina reads far more tropical and has always had panache to spare, and while it’s never been out of style with honeymooners, it’s enjoying a moment.
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Stay
Cambridge Beaches
Many of Bermuda’s legacy properties have been expanded or overdeveloped, but this one—the island’s original luxury resort from 1923—has been gorgeously updated without losing any of its original charm. It sits on a 23-acre peninsula with beautifully appointed cottages, four beaches, two private coves, an infinity pool overlooking the bay, and superb food at Breezes, a favorite among locals.
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Eat
Barracuda Grill was Michael Douglas and Catherine Zeta-Jones’s favorite, while Achilles is a chic cliffside place to watch the sunset. Mad Hatters is a fanciful little hideout, all with excellent food.
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The Bermuda Railway Trail is a gorgeous way to see the island for bike riders of any ability. Don’t forget to commemorate your wedding trip with signature scents from Lili Bermuda.
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Bar Harbor
Few places are equally beguiling, whether the sun is glinting off the gleaming hull of a classic sailboat or you can barely see the buoy off the end of the dock through the fog. Maine’s Acadia National Park has attracted Rockefellers and Fords for generations, but reinvented landmarks and shops selling more than just lobster- and blueberry-themed souvenirs have brought it decidedly into the 21st century.
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The Claremont
A landmark hotel that recently underwent a dramatic facelift, this Southwest Harbor institution is both a grande dame and the belle of the ball, thanks to a total update. In addition to exquisite décor and superb food and service, it has a Hinckley picnic boat for charter, a croquet court, and a pool with cabanas Ralph Lauren would plotz over. The secluded location is only 20 minutes from downtown Bar Harbor.
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Eat
The fact that a restaurant in Southwest Harbor is open 11 months a year is one indication of how good Red Sky’s locally inspired American cuisine is, while Brasserie Le Brun in downtown Bar Harbor gives fresh Maine ingredients a delicious French twist.
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Acadia National Park is one giant natural playground, but be sure to choose one morning to drive to the top of Cadillac Mountain and be the first people in the U.S. to see the sunrise.
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Nantucket
The sheer number of billionaires who choose to own homes here is only one indication of the Gray Lady’s endless charm. “Town” is the most picturesque Quaker whaling village in New England, with incredible shopping and restaurants, while the beaches are just the start of the stunning natural beauty.
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Stay
The Wauwinet
Remote and perfectly situated on a stretch of gorgeous beach, this five-star resort has regular water-taxi service into town, but you might not want to leave. Watching the sunset from the lawn is a daily ritual, and Topper’s restaurant has exceptional food and one of the best wine lists on the island.
Eat
Via Mare in the Greydon House serves local fare with a Venetian twist, while Straight Wharf Restaurant offers five-star food with spectacular views of the harbor. Its sibling clam shack is a casual waterfront spot that’s still worthy of a Michelin star or two.
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To feel like you’re walking through Candyland, stroll the Sconset Bluff Walk at sunset and watch the sherbet colors of the sky melt over cottages encrusted in roses.
First published in the print issue of Boston Weddings 2025 with the headline, “The Return of the Preppy Honeymoon.”
